The Business Casual Shoes I Can Actually Walk In (Yes, Even Over 50)

Every now and then, I get comments that ask for more “working gurl” outfits. I spend a lot of time working, but since I work from home, I don’t always think about typical office attire. When I think business casual, I want shoes that look polished enough for a business-casual outfit but don’t make me want to cry after an hour of wearing them.

Comfort and style can go hand-in-hand! These picks all have cushioned insoles, good structure, and a little personality. Perfect for a day at the office, running errands, or dinner out without needing a shoe change in your car (we’ve all been there). If you’ve ever struggled to find work shoes for women over 50 that feel as good as they look, I’ve rounded up a few favorites I can actually walk in, no break-in required.

• Summer Sneakers: Comfortable, Chic Picks for Women Over 50
• The Best Shoes to Wear with Wide-Leg Pants for Women Over 50

Comfortable Business Casual Shoes That Actually Feel Good

Quince Pointed Toe Ballet Flats

You can never go wrong with a timeless leather ballet flat. Think soft, buttery leather in neutral shades like beige, blush, or camel. These are perfect for work, casual outfits, or even travel days when you need a comfortable yet polished shoe.

• Classic style
• Neutral color that goes with everything
• Versatile enough to pair with dresses, jeans, or shorts

Eileen Fisher Leather Sandals

These Khaki Leather Sandals are comfortable right out of the box with a cushioned footbed that makes long days on your feet a breeze. The khaki shade is a neutral classic that pairs easily with any outfit. I have become a HUGE fan of Eileen Fisher shoes! I’ll admit, I was surprised that their shoes are so comfortable.

• Cushioned sole provides all-day comfort for sensitive feet.
• Neutral color elongates the look of your legs.
• Adjustable straps ensure a secure fit.

Sam Edelman Alie Ballet Flat

This little Ballet Flat comes in the prettiest colors for fall. There are a lot of options, including a fun blue version for a pop of color. I’m partial to this shade of brown this year, and my closet is already bursting with chocolate/cafe. These are lightweight and flexible; they are perfect when you want something simple but elevated.

• Soft leather upper
• Cushioned insoles for comfort
• Stylish color that freshens up neutrals

Sam Edelman Kasey Square Toe Ballet Flat

I love a square toe for something modern. These toffee suede Ballet Flat add a little bit of edge while staying elegant. They’re comfy and easy to dress up with trousers or down with jeans.

• Square-toe shape looks sleek
• Soft suede upper
• Flexible sole for easy walking

Loafers That Are Both Stylish and Supportive

Loafers are such a staple this time of year, and these business casual loafers for women offer everything from flexible soles to polished finishes. You can wear them with ankle pants, denim, or even a midi skirt and still feel pulled together.

Talbots Audrey Nappa Loafers

How luxe do these Nappa Loafers look! Made from nappa leather, they are made to mold to your feet. Wear them with slacks, ankle pants, or even jeans for a classic vibe. They’re called the Audrey. Do you think these are Audrey Hepburn inspired, maybe?

• Timeless, structured loafer design
• Padded footbed for all-day wear
• Great with both tailored and casual outfits

Sam Edelman Elaina T-Strap Buckle Loafer

I love that these are a bit rugged. Business casual doesn’t mean boring! These T-Strap Loafers are chic, unexpected, and comfy with their cushioned insoles. They would look fabulous with cropped pants or a great pair of dark denim jeans.

• Unique T-strap detail for extra style
• Suede finish adds texture
• Cushioned insole for all-day support

Old Navy Faux-Leather Pointy-Toe Loafer

Budget-friendly and super versatile, these Pointy-Toe Loafers look way more expensive than they are. They slip on easily, have a bit of structure, and the sleek shape works with slim pants or wide legs.

• Affordable and stylish
• Lightweight with a comfortable fit
• Easy slip-on design

Old Navy Faux-Leather Loafers

The chunky sole and heel keep these Loafers from being boring. Plus, they’re another very affordable option! Reviews are good with people saying they are comfortable and fit true to size.

• Simple design for casual outfits
• Comfortable to slip into for quick trips
• Great with cropped trousers or jeans

Affordable Work Shoes That Don’t Skimp on Comfort

If you’re looking for affordable work shoes that don’t sacrifice comfort, Old Navy has some surprisingly stylish picks. These are great for anyone building a business casual wardrobe on a budget.

Quince Leather Pointy Penny Loafer

You know that Quince is my fave! These loafers from Quince have that classic penny loafer style with a modern, sleek pointy toe. They’re made from quality leather, and the fit is tailored but flexible. I already own this Soft Leather Loafer that I wore all summer, so I think I need this pair for fall.

• High-quality leather upper
• Classic style with a modern silhouette
• Comfortable for all-day wear

Quince Leather Lug Sole Loafer

If you need a little more grip and edge, these Leather Lug Sole Loafers are perfect. They’re a little more expensive than the Old Navy version, but hey, they’re Italian leather! The bone color is fresh for fall and works with just about everything in your closet.

• Lug sole adds traction and trendiness
• Soft leather for a polished look
• Great paired with wide-leg trousers or slim jeans

These supportive shoes for office wear give you the best of both worlds: comfort and confidence. Whether you’re at your desk or dashing to an appointment, you don’t have to choose between style and stability.

FAQs About Comfortable Work Shoes

Q: What makes a shoe “business casual”?
Business casual shoes are polished but not overly formal. Think ballet flats, loafers, or low-heeled sandals that pair well with trousers or dresses.

Q: Are flats or loafers better for all-day wear?
It depends on your feet! Flats are lighter and more flexible, while loafers usually offer more support. If you walk a lot, loafers with a cushioned footbed are usually best.

Q: Can women over 50 wear trendy shoes?
Absolutely! Comfort doesn't mean boring. Many of these picks have modern shapes, colors, or details that keep your style current without sacrificing your feet.

Comfortable Work Shoes for Women Over 50: Final Thoughts

Finding the perfect pair of business casual shoes can be tricky, but these give you a solid mix of comfort, style, and versatility. I love that these stylish, comfortable flats don’t just look good, they actually feel good too. That’s something I never take for granted anymore! Whether you’re a loafers-all-day kind of gal, love a pretty flat, or need something easy to slip on, these shoes can handle your workday and still look good when you head out for dinner after.

Which ones are calling your name? Are you Team Loafers, Team Flats, or Team Both?

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